Jan Lennard Struff defeated Grigor Dimitrov 6-4 6-7 6-3 in the Rome Masters round of 64 on clay. The upset overturned the form book — Grigor Dimitrov came in leading the head-to-head 4–1, defending last year's round of 32, but Jan Lennard Struff had been the form player, winning 1 of their last 6 on clay. Jan Lennard Struff narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2023-03-20 | Miami Masters | R64 | hard | Grigor Dimitrov | 4-6 7-6(5) 6-4 |
| 2021-04-12 | Monte Carlo Masters | R64 | clay | Grigor Dimitrov | 6-3 6-4 |
| 2019-04-15 | Monte Carlo Masters | R32 | clay | Grigor Dimitrov | 7-6(2) 6-4 |
| 2017-04-17 | Monte Carlo Masters | R32 | clay | Jan Lennard Struff | 4-6 6-3 6-2 |
| 2013-10-14 | Stockholm | R16 | hard | Grigor Dimitrov | 6-1 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.